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L-脯氨酸置于palladium On Activated Charcoal 氢气,Potassium Carbonate体系中,用 乙醇,N,N-二甲基甲酰胺 用作溶剂,化学反应 12.0H,反应生成1-苄基-L-脯氨酸
参考文献:The First Enantioselective Total Syntheses Of The Allopumiliotoxin A Alkaloids 267A And 339B
标题:The First Enantioselective Total Syntheses Of The Allopumiliotoxin A Alkaloids 267A And 339B
摘要:Short,Highly Stereocontrolled,Asymmetric Total Synthesis Of The Title Amphibian Alkaloids Are Described. In The First Stage The Indolizidine Ketone 11 Is Assembled From L-Proline In Enantiomerically Pure Form. This Short Sequence Proceeds In Five Laboratory Operations And Involves The Novel Intermediacy Of An "Unprotected" 2-Acylpyrrolidine Intermediate (Scheme Vii). The (Z)-Alkylidene Side Chain Of The Target Alkaloids Are Introduced By Stereocontrolled Aldol Dehydration Sequences (Schemes X And Xi). These Enantioselective Total Syntheses Confirm The Structures And Absolute Configurations Of The Allopumiliotoxins 267A And 339B.
Doi:10.1021/jo00030A026

专利信息

专利号:WO-2016037298-A1
优先权日:2014-09-11
标题 :Method for the enantioselective synthesis of 2(s)-amino-6-boronohexanoic acid (abh) and purification thereof
发明人：PREITE MARCELO DANIEL; MANRIQUEZ MUJICA JUAN MANUEL; CORREA VARGAS JORDAN MAURICIO; ITURRIAGA AGUERA RODRIGO MANUEL; CASANELLO TOLEDO PAOLA CECILIA; KRAUSE LEYTON BERNARDO JAVIER
权利人:UNIV PONTIFICIA CATOLICA CHILE
摘要:The invention relates to a method for the enantioselective synthesis and purification of 2(S)-amino-6-boronohexanoic acid (ABH) and the preparation of the corresponding synthetic intermediates. The method comprises the preparation of ABH from BPB-Ni-Gly, which is treated with a strong base in a suitable solvent, and is made to react with 2-(4-lower bromoalkyl)benzo[d] [1,3,2]dioxaborol, where the lower alkyl is an alkyl with between 1 and 6 carbon atoms, preferably 2-(4- bromo-butyl)benzo[d][1,3,2]dioxaborol, while stirring, in a nitrogen atmosphere and with a cryogenic bath at a low temperature (-50°C), in order to then permit same to reach ambient temperature, removing the cryogenic bath, before neutralising in aqueous medium with a weak organic acid, and extracting with dichloromethane, drying the resulting organic extract which is subsequently filtered and vacuum evaporated. The resulting alkylated complex is dissolved in a C1-C5 alcohol, adding a hydrochloric acid, refluxing in a nitrogen atmosphere, and is subsequently cooled to ambient temperature, and concentrated in order to achieve the precipitation of (S)-2-[N-(N'- benzylprolyl) amino]benzophenone (BPB), as the hydrochloride salt, filtering and extracting with dichloromethane, and after dissolving the aqueous phase of the filtrate in water, it is treated with ammonia concentrated to pH 9, and once again extracted with dichloromethane, the ammoniacal aqueous phase being vacuum evaporated until dry, in order to produce crude ABH, as the ammonium salt, which is subsequently purified by means of ion-exchange chromatography. The invention also relates to a method for preparing the Gly-Ni-BPB complex, 2-(4- bromo-butyl)benzo[d][1,3,2]dioxaborol, which is used as an alkylating agent in the form of a borate side chain, and (S)-N- benzylproline (BP).

专利号:US-10030003-B2
优先权日:2014-09-10
标 题:Synthesis of isoflavanes and intermediates thereof
发明人：BELIAEV NIKOLAI; SHAFRAN YURI
权利人:SYSTEM BIOLOGIE AG
摘要:Subject of the invention is a method for enantioselective production of an isoflavane from an isoflavone, comprising the steps: (a) selectively reducing the isoflavone, such that the 4-keto group of the isoflavone is converted to a 4-hydroxy group, and the 2,3-double bond of the isoflavone is converted to a 2,3-single bond, thereby obtaining a 4-hydroxy intermediate, and (b) reacting the 4-hydroxy intermediate with a chiral reagent, such that a chiral group is covalently attached to the C4-position of the 4-hydroxy intermediate, thereby obtaining a chiral intermediate. The invention also relates to intermediates of formulae (IV), (V), (VI) and (VII) obtainable in the inventive process.

专利号:WO-2018178397-A1
优先权日:2017-03-30
标题 :N-alkylated amino acids and oligopeptides, uses thereof and methods for providing them.
发明人：BARTA KATALIN; YAN TAO; FERINGA BERNARD LUCAS
权利人:UNIV GRONINGEN
摘要:The invention relates to the synthesis of amphiphilic amino acid derivatives, in particular to a method for the N-alkylation of an unprotected amino acid or the N-terminus of an oligopeptide substrate, comprising reacting said unprotected amino acid or oligopeptide substrate with an alcohol, e.g. a fatty alcohol, in the presence of a homogeneous transition metal catalyst.

专利号:CA-2960437-A1
优先权日:2014-09-10
标 题 :Synthesis of isoflavanes and intermediates thereof

专利号:US-2017283389-A1
优先权日:2014-09-10
标题 :Synthesis of Isoflavanes and Intermediates Thereof

专利号:KR-20170054461-A
优先权日:2014-09-10
标 题 :Synthesis of isoflavanes and intermediates thereof